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Amides to Carboxylic Acids: Hydrolysis01:28

Amides to Carboxylic Acids: Hydrolysis

4.7K
Amides can undergo either acid-catalyzed hydrolysis or base-promoted hydrolysis through a typical nucleophilic acyl substitution. Each hydrolysis requires severe conditions.
Acid-catalyzed hydrolysis:
Hydrolysis of amides under acidic conditions yields carboxylic acids. Since the reaction occurs slowly, hydrolysis requires the conditions of heat.
The mechanism begins with the protonation of the carbonyl oxygen by the acid catalyst. The protonation makes the amide carbonyl carbon more...
4.7K
Nitriles to Carboxylic Acids: Hydrolysis01:08

Nitriles to Carboxylic Acids: Hydrolysis

5.4K
Nitriles undergo acid-catalyzed hydrolysis or base-catalyzed hydrolysis to form a carboxylic acid. These reactions proceed via an amide intermediate.
5.4K
Acid Halides to Amides: Aminolysis01:07

Acid Halides to Amides: Aminolysis

4.6K
Aminolysis is a nucleophilic acyl substitution reaction, where ammonia or amines act as nucleophiles to give the substitution product. Acid halides react with ammonia, primary amines, and secondary amines to yield primary, secondary, and tertiary amides, respectively.
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...
4.6K
Preparation of Amides01:29

Preparation of Amides

4.3K
Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
4.3K
Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

3.7K
Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
3.7K
Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

4.8K
Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
4.8K

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Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
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DNA触媒によるアミド水解

Cong Zhou1, Joshua L Avins1, Paul C Klauser1

  • 1Department of Chemistry, University of Illinois at Urbana-Champaign , 600 South Mathews Avenue, Urbana, Illinois 61801, United States.

Journal of the American Chemical Society
|February 9, 2016
PubMed
まとめ
この要約は機械生成です。

研究者らは,タンパク質のような機能群を組み込むことで,アミド水解のための新しいDNA触媒 (デオキシリボ酵素) を開発した. この画期的な発見により 新しい生化学的応用のための 人工タンパク質が作れるようになりました

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科学分野:

  • 生物化学
  • 分子生物学
  • 合成生物学

背景:

  • DNA触媒 つまりデオキシリボ酵素は 様々な化学反応の 強力なツールです
  • アミド水解のためのデオキシリボ酵素の特定は困難であり,以前の試みは異なる触媒的活動をもたらした.

研究 の 目的:

  • アリファティック・アミドの水解を触媒にできるデオキシリボ酵素を開発する.
  • デオキシリボ酵素の能力を拡張するために,タンパク質のような機能群を持つ改変核酸の使用を調査する.

主な方法:

  • 新型デオキシリボジームを特定するために,in vitro選択を用いた.
  • 主要なアミノ基,カルボキシル基,または主性ヒドロキシル基を持つ改変した核酸はDNA配列に組み込まれました.
  • 選択戦略は,特にリン酸エステル溶解よりもアミド溶解をターゲットに設計された.

主要な成果:

  • 改造された核酸の組み込みにより,アミドを水解するデオキシリボ酵素の識別が成功しました.
  • 特定されたデオキシリボ酵素は,ニュクレオチドの改変なしに,有意な触媒的活性を維持した.
  • この研究は,デオキシリボ酵素の新しい触媒的機能の発見におけるタンパク質のような機能群の有効性を実証した.

結論:

  • タンパク質のような機能群を持つ改変した核酸は,アミド-水解性デオキシリボジームの識別に不可欠である.
  • これらの発見は,将来の応用のための人工プロテアゼとしてのデオキシリボ酵素の可能性を強調しています.
  • 機能群を組み込む戦略は,他の新しいデオキシリボ酵素の活動を発見するために適用できます.